Cu-Catalyzed [4+1] Annulation toward Indolo[2,1-a]isoquinolines through Oxidative C(sp3)/C(sp2)-H Bond Bifunctionalization

被引:15
作者
Zhang, Tian-Shu [1 ]
Zhao, Qi [1 ]
Hao, Wen-Juan [1 ]
Tu, Shu-Jiang [1 ]
Jiang, Bo [1 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China
关键词
carbonylation; copper; organic chemistry; oxidation; synthetic methods; RECEPTOR-BINDING AFFINITIES; ALPHA-DIAZO CARBONYLS; H BONDS; C(SP(3))-H BONDS; TANDEM SYNTHESIS; ACTIVATION; CONSTRUCTION; ADJACENT; NITROGEN; FUNCTIONALIZATION;
D O I
10.1002/asia.201900050
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Cu-catalyzed [4+1] annulation of N-aryl-1,2,3,4-tetrahydroisoquinolines (N-aryl THIQs) with alpha-diazoketones has been established under oxidative conditions, leading to the construction of a series of indolo[2,1-a]isoquinolines with generally good yields. The reaction enables dediazotized dicarbonylation of alpha-diazoketones, creating direct C(sp(3))/C(sp(2))-H bond bifunctionalization to access tetracyclic aza-heterocyclic skeletons.
引用
收藏
页码:1042 / 1049
页数:8
相关论文
共 82 条
[1]   High mobility single-crystal field-effect transistors from bisindoloquinoline semiconductors [J].
Ahmed, Eilaf ;
Briseno, Alejandro L. ;
Xia, Younan ;
Jenekhe, Samson A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (04) :1118-+
[2]   Ni(II)-Catalyzed Oxidative Coupling between C(sp2)-H in Benzamides and C(sp3)-H in Toluene Derivatives [J].
Aihara, Yoshinori ;
Tobisu, Mamoru ;
Fukumoto, Yoshiya ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (44) :15509-15512
[3]   SYNTHESIS AND ANTITUMOR-ACTIVITY OF METHOXY-INDOLO[2,1-A]ISOQUINOLINES [J].
AMBROS, R ;
VONANGERER, S ;
WIEGREBE, W .
ARCHIV DER PHARMAZIE, 1988, 321 (08) :481-486
[4]   INDOLO[2,1-A]ISOQUINOLINES - SYNTHESES, STEROID-HORMONE RECEPTOR-BINDING AFFINITIES, AND CYTOSTATIC ACTIVITY [J].
AMBROS, R ;
SCHNEIDER, MR ;
VONANGERER, S .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :153-160
[5]   VYNYLOGOUS CARBINOLAMINE TUMOR INHIBITORS .23. SYNTHESIS AND ANTILEUKEMIC ACTIVITY OF BIS[[(CARBAMOYL)OXY]METHYL]-SUBSTITUTED PYRROLO[I,1-A]ISOQUINOLINES, PYRROLO[1,2-A]QUINOLINES, PYRROLO[2,1-A]ISOBENZAZEPINES, AND PYRROLO[1,2-A]BENZAZEPINES [J].
ANDERSON, WK ;
HEIDER, AR ;
RAJU, N ;
YUCHT, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (11) :2097-2102
[6]  
[Anonymous], 2011, Angew. Chem
[7]  
[Anonymous], 2009, ANGEW CHEM
[8]   Gold(I)-Catalyzed and H2O-Mediated Carbene Cascade Reaction of Propargyl Diazoacetates: Furan Synthesis and Mechanistic Insights [J].
Bao, Ming ;
Qian, Yu ;
Su, Han ;
Wu, Bing ;
Qiu, Lihua ;
Hu, Wenhao ;
Xu, Xinfang .
ORGANIC LETTERS, 2018, 20 (17) :5332-5335
[9]   Formal Allylic C(sp3)-H Bond Activation of Alkenes Triggered by a Sodium Amide [J].
Bao, Wei ;
Kossen, Hanno ;
Schneider, Uwe .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (12) :4362-4365
[10]   SYNTHESIS OF (+-)-CRYPTOWOLINE IODIDE [J].
BENINGTON, F ;
MORIN, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (04) :1050-+